


Transportation

by TheManWithTheHood



Category: Once Upon a Time (TV)
Genre: Adult/Teen Incest, Bathroom, Bathroom Sex, Dry Cum, Dry Orgasm, Exploration, First Time, Glory Hole, Humor, Incest, M/M, OC, OC Incest, Oral, Orgasm, Pre-pilot, Sloppy Cum, Strangers, This is the story of how Henry Mills got from Maine to Boston, Totally consenual but not at all legal, Voyeurism, cum, gas stations, mostly innocent exploration, teaching blowjobs, train, transportation
Language: English
Status: In-Progress
Published: 2015-04-02
Updated: 2016-06-16
Packaged: 2018-03-20 21:34:33
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 8,589
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3665958
Author URL: https://archiveofourown.org/users/TheManWithTheHood/pseuds/TheManWithTheHood
Summary: <blockquote class="userstuff">
              <p>Henry Mills made the journey from a coastal Maine town to Boston, MA in one day.  How did he do that?  Well - now we know.  He had some help, and learned a few things along the way.</p>
            </blockquote>





	1. Probably Hitch Hiking

**Author's Note:**

> Hey all, so I get a lot of prompts on tumblr, and this was one of them. I'm using this AO3 account to post the more weird/odd tumblr prompts.  
> I will also accept prompts here by the by!

     It had never been like this back in Storybrooke. Outside the confines of his town, Henry felt very small and unprotected. Never the less he put on a brave face and soldiered on to find his birth mother – Emma Swan. He had left early in the morning, 5’o’clock-ish, and had gone on foot to Ellsworth, a town a few miles away. He’d arrived around 7:40, starving, and ducked into the first gas station he saw. He needed food, drink, and the bathroom.

     Moments later he emerged from the mens restroom, and headed over to the snacks. He grabbed a package of twinkies, some beef jerky, and an orange. Regina had taught him to balance out his meals. He grabbed a water and a Gatorade and lugged it up to the counter. The pimply faced cashier had been staring at Henry through half closed eyes since the ten year old had arrived, and dutifully rang up the exhausted boys order.

     “7.96” the cashier says in a half-asleep monotone. Working the early shift was absolutely the worst thing to ever happen in this teenagers life. Henry fished out a ten and handed it over to the other boy.

     “Hey. Can you tell me where the nearest bus station is?” The teen blinks at Henry for a moment before shaking his head. Henry frowns and looks around for a moment. “Do you guys sell maps?” The teen sighs and points to a stand near the door, Henry turns and smiles at the customer behind him apologetically and goes to pull out a map, he quickly checks for stations and frowns, before putting the map back and retrieving his change, and food. “Thanks. Have a good day!” The teen grunts and waves as Henry darts out of the store. The teen turns back to the register.

     ****“Can I help whose next?”

     There is silence, so the teen looks up, the customer behind Henry had left his items on the counter and walked out. The bell on the door still ringing faintly. The cashier silently thanks a deity and ducks out from behind the counter to grab a coffee, not giving a second thought to the strange boy and man.

     Henry plods along outside, shifting his backpack uncomfortable from shoulder to shoulder, he was disheartened to learn that the nearest bus station was still going to be another hour on foot, and the train station (which he really wanted to get to) was an hour and a half. At this rate he wouldn’t get to Boston until the Wednesday after next.

     “Hey kid -”

     A clear baritone voice calls out to Henry, who pauses and turns to see the man that had been behind him in the gas station quick walking to catch up to him.

     “Yeah?”

     “You need a lift to the bus station?”

     The tall man jerks his thumb back to a small silver car, resting in one of the parking spaces. Henry rolls his eyes, he knew better than to get in a car with a stranger.

     “Well, what I really need is a lift to Boston – but I don’t think I can –“

     The man starts to chuckle and then breaks out into a full laugh, it was almost unnerving to Henry, who looked over at the man with a tentative expression on his face.

     “Oooh. Sorry – no I’m not going to Boston. I can’t get you there – but you sound like you need to go to the train station. I can get you there –“ The man checks his watch – “In time for the 9:10 train.”

     Henry pauses. That would certainly cut down on his travel time by a solid six hours. He’d get into Boston at noon, and then he could track down Emma before dinner. He carefully weighs those options and slowly unclenches his back.

     “I can give you gas money… but I’m warning you. I have a cellphone – and I’m not afraid to use it.”

     The man lifts his hands into the air in mock defeat.

     “Oh no, my master plan is revealed. No – I’m kidding. Gas money not required, I’m headed to the station to pick up my cousin. You can ride in the back, or the passenger’s seat. Whatever makes you comfortable.” The man starts to turn back to his car – before pausing. “Oh I’m sorry, hi, I’m Jude.”

     “Henry.”

     The two head to the car, and Henry clambers into the back seat, pulling the buckle across himself. As the man climbs into the drivers side, Henry fidgets. As the two pull out of the gas station, Henry exhales sharply. He shouldn’t have gotten into a strangers car, it’s not safe… Henry whips out his cellphone, ready to dial when Jude spies him in the rearview mirror.

     “Hey kid, if you want to get out, I can pull over. I don’t need the cops ramming themselves up my tailpipe.”

     Henry blinks a little and looks back at Jude – before slowly pocketing the still active cellphone.

     “You gonna be okay?”

     Henry nods.

     “Cool. If it makes you feel better you can hold the GPS and make sure I don’t go anywhere that isn’t the train station.”

     Jude tosses the device back at Henry, as they continue on down the road.

\----------------------

            Jude had been chatting away amicably at Henry for the past 15 minutes, on the way to the train station. He didn’t expect the kid to say much – he knew he certainly wouldn’t if he had been picked up by a strange man at a gas station. Well, maybe. Anyway, he got a few answers from Henry, but mostly the young boy had remained silent through the ride.

            “How far out are we from the station Henry?”

            “About 20 minutes.”

            “Cooleo.”

     Then the silence fell in the car. Jude had divulged all he felt like he wanted to, and Henry didn’t want to initiate a conversation – so the ride was silent for a good 2 or 3 minutes before Henry, unable to take the deafening stillness anymore, found something to talk about.

     “That’s a… uh… a nice scarf.”

     Henry was of course referring to the candy cane striped scarf that rested around Jude’s neck – it clashed a little with the grey hoodie the man wore, but none the less it looked good.

     “Oh thanks. It was a gift from my uncle. He said it suited me… I used to dress really spiffy when I was a kid, I had a lot of over coats, and nice clothes, kinda like the jacket you’re wearing now… I still dress up from time to time, but I finally realized I didn’t need to show off my _fabulous_ side every time I went out.” Henry giggled and Jude guaffed at his own joke. The car dinged quietly and Jude _tsk’d._ “Hey Henry, I think we gotta pull into a gas station. I didn’t realize it was going to take this long.”

     “Didn’t you pick me up at a gas station?”

     “Yeah – but I didn’t get gas. I was getting some snacks… which I also forgot to buy.”

     Henry goes quiet for a moment, as the two pull into another chain gas station.

     “If you want you can wait in here, or you can head inside, or you can do whatever. I ain’t yer dad.” Jude pops out and plugs his card into the pump, slowly filling up the tank. Henry quietly pops out of the car and looks back at Jude.

     ****“I’m just gonna use the bathroom.”

     Jude nods

     “I won’t leave without ya, unless y’ask me to.”

     Henry smiles tightly and runs inside, he left his backpack behind in the car, to signify his intent on returning.

\--------------------------------------------------------

     Henry pushes the door open and clicks the one man restroom shut behind him. Locking it to be safe – he had finished off his Gatorade and water and _really_ had to go, now that he didn’t have pressure on his bladder.

     As Henry is finishing relieving himself there is a sound of metal scraping against metal that sends a shiver up Henry’s spine. “ _What was_ that _?”_ He whispers to himself, the sound rings through the small bathroom again and Henry realizes that it’s coming from the metal panel beside the toilet. Henry tentatively touches the cold metal, and the sound happens again, with his fingers pressed against the metal, Henry realizes that something is moving the other side of the panel on the outside. Upon closer inspection of the panel, Henry sees that there is only one solitary screw left to hold the metal in place, and slowly untwists it, pulling the panel off the wall. The other side of the panel is still in place, so Henry reaches through the small hole, and taps on the metal slowly. The panel swings upwards, as if someone were greedily pulling the panel away from the wall, and a blast of the cold outside air comes through before something plugs the hole in the wall. Henry had stepped away from the wall when the cold air had blasted through, but was now mesmerized and almost terrified by what had taken the hole’s place.

     “What the hell!?” Henry exclaims, less terrified now, and more confused and angry – for there was a very large, very veiny dick protruding from the wall. “I mean seriously!? What the hell are you doing!?”

     There is a muffled exclamation by a gruff voice outside.

     “Oh shit – it’s a _kid_.” The dick quickly retracts and the hatch slams shut – Henry scrabbles for the metal plate, and slams it back into place, screwing the screw in. He wishes he had a marker to write ‘beware – penises on the other side’ on the metal, but he left all those in the car.

     Henry quickly pulled himself up to his full height and started to go for the door, before realizing he had yet to wash his hands, or zip himself up. Neither of which would be hygienic to go outside without doing. He pushed his own dick back into his jeans, wondering why they were now so tight. That usually only happened when he needed to use the restroom, but he had already done that. His face flushed he was his hands and exited the bathroom – ignoring the burly man that was (very obviously) avidly avoiding him in the store.

     Henry storms out of the store and heads very quickly back into Jude’s car, Jude has just finished up at the pump and gets into the car with a puzzled expression on his face.

     “You okay kid?”

     “Yeah, I think. Maybe.”

     Jude gives him a look before something clicks into place.

     “Uhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh – does your dour expression have anything to do with the shouting trucker a few seconds ago?”

     Henry shifts uncomfortably in his seat – avoiding looking at Jude’s face.

     “Maybe.” Jude is torn between laughing hysterically and comforting the kid. It transformed into a snort sneeze, that startled Henry, who glares at Jude, before blushing even harder and opening the car door. “I think I’m going to walk the rest of the way to the station.”

     “No, no, Henry, _wait_.” Jude reaches his hand back and gently grabs Henry’s arm, trying to be as non-threatening as a 6’4’’ man can be. “Sorry – it’s just. I was not in any way mentally prepared to hear that. Are you okay?” Henry calms for a moment, removing his hand from the handle of the car, and sitting back in his seat.

     “Yeah. I think so… I’m just kinda… freaked out.”

     Jude bites his lip and nods.

     “Yeah, surprise dicks’ll do that do a person.”

     “It’s not funny!” Henry retorts kicking the back of Jude’s seat. “Isn’t this the sorta thing that scars kid’s for life!?”

     “Well _maybe_ if you let it get to ya. Come on – you’ve seen one penis, you’ve seen ‘em all.” Jude starts the car and pulls away from the station, about a minute in the silence, Jude realizes something and looks back at Henry. “You _have_ seen another penis before. _Right_? That wasn’t your first time seeing someone else’s magic stick.” Henry avoids looking Jude in the eyes. “Didn’t you ever see your dad’s? A brother’s? Didn’t you ever go, like, swimming with a friend and accidentally see his or something?” Henry clears his throat and looks dead into Jude’s eyes.

     “I am adopted… by a single mother. And I live in a _very_ small town. There are _maybe_ two boys my age, and I don’t know either of them well enough to get invited swimming, let alone see their… _penis_.” Jude makes a mock embarrassed face and glues his eyes to the road. Henry looks away finally, red still tinging his cheeks.

     “Was it big?”

     “WHAT!?!?” Henry almost hit soprano with his screech, the red flushing back to his cheeks. Jude laughs hysterically. “Why would you _ASK_ THAT!?”

     “Because I knew you’d jump like that.”

     “WELL DON’T.”

     “Okay. Fine – I’ll drop it.” A few more minutes pass in silence as they keep on down a slightly busier road. Just as Henry gets comfortable again Jude smirks.

     “Was it _hairy?_ ”

     “OH MY GOD!” Jude devolves into laughter again – Henry is really steaming at this point and just lets a torrent fly forth. “Do you _really_ need to know? Sure! Fine! Whatever! It _was_ big! It was weird! It was like, longer than a sub! Okay? A-and thick and massive like that polish sausage! GOD DAMNIT now I’m NEVER GOING TO BE ABLE TO EAT KIELBASA AGAIN. And I don’t know! Maybe it was hairy! Maybe not!? I didn’t STOP. TO. CHECK!” After Henry’s rant, Jude clicks on the turn indicator and pulls the car over to the side of the road. “Why are you pulling over?”

     Jude pauses a moment, and devolves into the strongest most hysterical laughter anyone has ever had, he is as bent over as he can get in the driver’s seat and almost sobbing into the seat. Henry fumes in the backseat, all pretense of actually getting out gone. Jude finally stops laughing, and looks back at Henry.

     “Jesus kid. You’re really p-passionate about t-that penis.” Jude wheezes out a little bit more laughter, and Henry rolls his eyes. “Seriously, like, the size of a sub? You didn’t stop to check if it was hairy, but it was the length of a s-s-s-sandwhich? Pffft.” Henry angrily shifts in the backseat. “You know the average is probably, like, 5 inches or something right? Christ. I can’t believe it. You probably just saw, like, the _most average penis_ , and you’re freaked right the f-uh-hell out.” Henry finally snaps.

     “It was big and it was weird, and I didn’t know how to process it. Maybe if I’d like, _seen it on my own terms_ , I mighta been fine. I don’t appreciate you turning it into this big joke.”

     Jude quiets for a moment and shakes his head.

     “Alright – I’m mostly sorry. I’ll stop making fun of you for getting freaked out by a glory hole. I’d have probably jumped a few feet if I didn’t know the hole was there and then suddenly, _penis_.”

     Jude turns on the indicator and pulls back into traffic while Henry twiddles his thumbs.

     “I, uh, kinda went looking for the hole actually.”

     Jude nearly slams on the brakes.

     “You _went looking for a glory hole_ , but _you’ve never seen a penis before_?”

     Henry shakes his head vigorously.

     “I – I – I don’t even know what a glory hole really _is!_ Okay? I just heard scraping on one side of the wall, and wanted to know why, so I moved this metal bit, and then there was a hole, and _bam_. Penis.”

     Jude exhales slowly.

     “So, really you were just as surprised as if the dick had suddenly appeared. You didn’t go looking for the hole.”

     “No.”

     Jude nods and shrugs, and Henry shifts in his seat again, picking absentmindedly at the front of his jeans which had once again gotten tight. It was _possible_ he needed to pee again, but not likely. A minute or two passes before he looks up at Jude questioningly.

     “So, what’s a glory hole?”

     Jude nearly slams on the brakes again.

     “Jesus kid, you can’t just… ask that. You _know_ what a glory hole is. You _saw_ one.”

     “No, I mean, like, okay, I _get_ that guys put their penises into the hole. But _why?_ ”

     Jude pauses and turns to look at Henry, picking at his pants.

     “The same reason you’re doing that.”

     “Doing what?”

     “Aw. Christ kid. Alright – you _really want to have this conversation?_ ”

     Henry squints defiantly, now he had the power.

     “Yeah. I do. Why do guys stick their penises into the glory hole, and what does it have to do with me?”

     Jude shrugs – defeated. It wasn’t his kid.

     “Guys stick their dicks through the hole to get ‘em sucked on. Or rubbed on. Which is why it relates to you, that’s what your hand is trying to do to yourself right now.”

     Henry tenses his whole body.

     “Suck. On. A. Penis?”

     “Yup. People do it _all_ the time.”

     “Doesn’t that taste – _gross!?_ ”

     “It depends on whose penis it is, a strange trucker at a bus stop _probably_ has a terrible dick. I, personally, wouldn’t want to suck on one of those.”

     “You sound like you’ve sucked on a penis before.” Henry says suspiciously, he watches as a small bead of sweat forms on Jude’s brow.

     “Well – yeah. Kinda. I’m gay, so, you know. I’ve, uh, had sex with dudes.”

     “Wait I thought sex was, like, naked wrestling to make a baby.”

     “Common… misconception… uh. So I’m not, like, super comfortable with talking about this with a 10 year old.”

     “Too bad. You brought it up… So what _is_ sex then?”

     “Damn… uh. Fine, fuck it, sorry for the swear, whatever. Sex is what two people do to each other when they either really like each other, or are bored, sometimes strangers do it because it feels good… Usually it involves the junk in other people’s trunks. Butts, dicks, if you’re into girls you’ll probably like boobs and puss-I mean vagina.”

     Henry is still squinting at Jude, letting all the clogs click into place.

     “So – sex. Is like. A sport.”

     “Kind of.”

     “A sport that people play with one other person?”

     “Doesn’t have to just be one…”

     “And it has to do with the other persons genitals. And your own… I thought you had to kinda mash ‘em together?”

     “In boy on girl sex that’s normally how it happens yes. But then there’s handjobs, blowjobs, rimming, anal, foreplay, blah blah blah. It’s a bunch of different flavors, but it all boils down to three simple questions.”

     “Which are?”

     “Is it consensual?”

     “Huh?”

     “Does everyone involved _want_ to be there and _want_ to be having sex? Consent is important kid.”

     “Okay. What’s the second one?”

     “Is it _safe_?”

     “Wait. Sex isn’t safe?”

     “Fuck it, kid, come on. You’re killing me here. Okay, fine, no, sometimes sex _isn’t_ safe. There are these diseases that can only infect other people through sex, or sometimes something that one person wants to do, isn’t safe to do with the other person. Like hitting them or something.”

     “That’s not safe at all.”

     “Exactly.”

     “Number three, and arguably the second most important question. Does it feel good?”

     “Huh.”

     “Yep.”

     The car falls silent, the GPS speaks up quietly. _Destination in, 3 miles_.

     “When do people normally learn this stuff?”

     “Uh – some of it’s taught in school. Some people pick it up through the internet, some pick it up on the streets, or _some_ , as we’ve learned today, learn it from strangers in a car.”

     Henry nods, and goes quiet for a minute.

     “Is that why stranger danger is a thing?”

     “ _Yes_ ”

     “Because they don’t want us learning about sex?”

     “ _Nooo._ ”

     “Then what?”

     The car is parked at a red light, as Jude brings his head down to meet the rim of the steering wheel. He was just making fun of the kid for being spooked, and now he was a 19 year old sex life guru to a prepubescent nerd.

     “Okay, so remember the first question.”

     “The everyone wanting the sex one?”

     “Yes. That one – okay – see – there are laws in place that say that _kids_ , no matter how much they may know, _aren’t supposed to have sex_. Even if they SAY ‘yes I want to have sex’ it is still illegal, and blah blah blah. The government _keeps_ it that way by not teaching kids about sex at all, until they’re like 12 or some bullshit. When trust me, most of them find out among themselves LONG before that.”

     “Uh-huh”

     “Anyway, most kids don’t know about sex, so they _can’t_ say yes, and there are creeps out there who like to lure people into vans and have sex with people, not just kids, without the persons permission.”

     “Ew.”

     “Exactly.”

     “That sounds gross.”

     “Yes.”

     “But what if, the kid, said. Yes?”

     “Still illegal.”

     “But is it _gross?_ ”

     “Some say yes.”

     “You?”

     Jude rolls his eyes as the two pull into the train station, he parks and turns to look at Henry.

     “Look – I started having sex when I was younger than you. Because I was a little piece of shit, and learned about it online before anyone had a chance to tell me what I was doing, or teach me anything. So – no, I don’t think having sex consensually with a kid is gross. But I _do_ think that, it needs to be a case by case basis. Just because a kid goes up to someone and says ‘hey I know about sex,' doesn’t automatically mean _go ahead and have sex with that kid_.  It would be a little easier if the person in question said 'hey I know about sex, about all the possible consequences, but I trust you enough to have sex with you’.  That's a _little_ better."

     “Didn’t you say strangers have sex?”

     “ _Sometimes_. And usually while drunk.”

     “Oh.” The two wait in the car, staring at the empty train rails. “Have you ever had sex with a kid? Like, as a grown up?”

     Jude nearly crashes the parked car.

     “No. Not really. I mean – look. Okay, no I have not actually had sex with a kid since I was 14, and even then we were only two years apart. It’s been all my own age or older for me since then. I’m just not attracted to kids, which I guess is a good thing. My cousin, actually the one pulling in, in a few minutes, was curious last year and asked if he could take a peek and feel around. He did, and that was kinda the end of it. We’d seen each other naked plenty of times before that – it was just an innocent exploration on his part.”

     Henry nodded, realizing he had started to pick at the front of his jeans again.

     “So – this sex thing. You can do it to yourself?”

     “Yeah, you wrap your hand around your dick and you pull up and down, the skin on your dick simulates sex, and then you cum.”

     “Come?”

     Jude sighs heavily, resting his head in his hands. “It’s the stuff babies are made out of. You don’t usually make it ‘til you’re older, like 14-ish, but I knew a kid when I was growing up that was full on cumming at age 11.”

     Henry nods wisely, this time not stopping the picking on his jeans.

     “Can I… uh… innocently explore?”

Every nerve in Jude’s body explodes simultaneously – Henry was almost no different, He’d just asked an almost stranger if he could take a peek at his junk.

     “Henry I don’t think, that, that’s a good idea.”

     “I don’t care if it’s a good idea. I want to _see_ … I mean... please?”

     Jude drums his fingers on the wheel for a moment, before pulling the key from the ignition and stepping out of the car.

     “Fine. Follow me – there’s a family restroom in the station.”

     Henry nods solemnly and grabs his backpack, following Jude into the station.

\----------------------

            Jude and Henry wait passively by the door to the family restroom, there’s a poor man in there changing a set of twins at the moment, and Jude decided they could wait. He lays a hand on Henry’s shoulder, heavily.

            “Stop touching the front of your pants – it’ll attract people’s attention. You already look too old to be followed into the bathroom by a family member.” Henry stops picking at his jeans, and folds his hands behind him, rocking back and forth nervously. “Remember, if you ever feel uncomfortable, just tell me, I’ll zip up and we’ll go our separate ways.” Henry nods quickly.

            The door opens and the poor father pulls the twins out of the bathroom with a haggard expression on his face. Henry slips into the bathroom first, unnoticed by anyone in the station, then Jude follows, casting a small glance around. No one seems to have noticed him entering the family restroom, and so he closes the door, and locks it in place.

            Henry is standing awkwardly in the middle of the room rocking back and forth on the balls of his feet, looking at Jude expectantly. Jude bites his lip, and sighs. This _really_ wasn’t an ethical idea. If _anyone_ found out… Jude unzips himself, and very slowly undoes the button, opening the front of his jeans, and pulling out his flaccid penis for Henry to gaze at.

            Henry stares, mouth agape, eyes bugging out of his head. He feels his own penis twitch and casts a glance down at himself, and starts picking at the front of his jeans.

            “Oh come on man. Don’t make this weirder than it is.” Jude says, blushing and looking away, Henry slowly lowers his hand and inches forward, kneeling down to get a better look at the slightly discolored skin.

            “It’s a lot darker than the rest of you…” Henry states breathlessly.

            “Yeah. That’s what happens when you rub something a lot – especially skin. It gets darker.” Henry nods solemnly, putting that fact away in the back of his mind. Suddenly the smell of Jude’s crotch hits Henry’s nose and he pulls back, not repulsed, just surprised. It’s a sharp, but heavy scent, unlike anything Henry’s ever smelled before. He leans forwards again and gingerly reaches out to touch Jude’s penis. “Whoa nelly, you don’t have to touch it.” Henry nods, but touches the middle of the penis gently, the warmth of the flesh sending chills down Henry’s spine. He imagines sticking it in his mouth and his pants twitch again, he reaches down with his free hand to rub at the front of his jeans this time instead of pick. “Henry…” Jude starts, but gets quiet, when Henry wraps two fingers around Jude’s moderately thick dick. “Oh my god.” Jude says as Henry tugs forwards, Jude’s dick slowly starts moving in the general direction of hard, as Henry watches in amazement. He barely touches the dick as it arcs it’s way upwards, ready for whatever comes next. Henry watches the uncut foreskin pull back over the glans, leaving them engorged and shiny, he watches a few veins appear along the shaft of the dick, and he watches the head itself flare, ready for anything.

            “Cool.” Henry whispers to himself, very gently running his hand along the shaft. Once he gets to the base he uses the knuckle measuring system his mother taught him when he was young, and counts. “1, 2, 3, 4, 5, 6, 7, 8!” Henry’s eyes bug out of their sockets. “You’re 8 inches long!? That’s huge!” Jude shakes his head, and moves Henry’s hand away from his shaft.

            “I am _not_ 8 inches long, sorry kiddo. You’re not that lucky. I’m 6 inches, 6 and a half a most, but that’s only after a couple months of not getting it on.” Henry looks down at his knuckles and frowns, he counts again, getting only 7 this time and shakes his head.

            “I must be doing that wrong.” Jude shrugs and stares up at the ceiling, until Henry wraps his hand around Jude’s shaft and squeezes, which almost brings Jude to his knees.

            “Damn it Henry, warn me before you do that.” Jude hisses through clenched teeth, Henry blushes and pulls his hand away, unsure of what to do now, although he has yet to stop rubbing himself through his jeans. “Okay, are you done?” Jude goes to fit his dick back into his boxers, but Henry grabs his wrist.

            “Uhm. Can I see, all your down below? Like the little dangly things? And your butt?” Henry blushes just saying that, but Jude sighs and nods, he tucks himself in, and sits down on the toilet seat, much to Henry’s dismay.

            “Calm down, if I’m showing you everything, I’m taking my pants all the way off, which means, shoes need to come off.” Jude tugs off his shoes, and then drops his jeans, scooting them away, and finally he drops his boxers, kicking them over with the other clothes. “Anything else you want me to take off Mr. Master?” Henry nods and motions to the jacket, scarf, and shirt. “Christ kid. I’m gonna freeze to death in here. Fine.” Jude unzips his hoodie, tossing it away, and removes his scarf, placing it gently on the edge of the changing table, before pulling off his t-shirt and unceremoniously dumping it on the ground with the rest of his clothes. The only clothes left on Jude are his socks and glasses, neither of which he intends to remove. “Happy now?” Henry merely nods and drinks Jude in, whilst still kneading his own erection.

            Jude stands at 6’ 4” with a little bit of weight on him, that shows in the belly, he’s thick necked, thick armed, and thick legged, either from muscles or bone structure, he is covered in dark hair, which is odd, considering the mop on his head is a dusty blond. Henry scoots closer, and looks at the dangling ball sack, poking it, causing Jude to flinch.

            “Watch it kid, those are sensitive.” Henry silently apologizes, and very gingerly runs his hand over them.

            “So – these get… bigger too?”

            “Yeah… just about everything gets bigger.”

            “Will everything get hairy too?”

            “It varies from person to person… my family could pass as a pack of werewolves sometimes, but something tells me your family with be very fair skinned.”

            Henry runs his hand over Jude’s balls once more before sitting back on his feet, mesmerized by the real life dick in front of his face. Henry’s hot breath was keeping Jude nice and hard for the whole thing. Henry thinks about it, slowly envisioning trying to put Jude’s dick in his mouth. Would it taste like it smells? Salty and heavy? Maybe it _would_ taste like Kielbasa. Henry’s mouth shoots up and he tries to engulf the penis before him, he barely makes it past the head, before he realizes he doesn’t have his mouth wide enough to fit anything in.

     “AH! God!” Jude jumps back, Henry’s teeth had scraped just enough against his glans to make it hurt. “Don’t – _do that_. You don’t know what you’re doing Henry.” Henry looks up at Jude with a pleading expression.

     “Teach me then! I can learn, I like this, I’m saying yes, and we’re safe!” Henry pleads - looking at the still tense Jude.  Jude slowly lowers his defenses, whilst still remaining tense, every alarm bell in existence was going off in Jude's head.

     “Are you _sure_?” Henry nods without a second thought and scoots towards Jude again, Jude holds up and hand, and reaches down to pull Henry into a standing position. Jude pecks Henry on the nose, before tugging off Henry’s heavy over coat, and pulling the boys shirt from his pants, and unbuttoning each button from the bottom, once Henry was shirtless, he stepped back to admire the mildly athletic build the boy had. Henry still retained a bit of his childish baby fat here and there, specifically in the stomach and breast region, but he was by no means chubby. Jude smiles and peppers kisses down Henry’s neck, whilst falling to his own knees, and down Henry’s front before reaching his belt.

     Jude unclasps Henry’s belt, pops the button, and shimmies the stubbornly tight jeans off of the 10 year old, leaving him in nothing but skewed super hero briefs, and mismatched socks. Henry blushes and tugs at his underwear, the tent standing out severely in the front.

     “I… I like Batman and Robin…”

     Jude smiles.

     “So do I, kid. So do I.”

     Jude kisses Henry’s belly button, and trails down the soft invisible happy trail to the top of the boxers, the tent barely poking his chin, he tugs and tugs on the waist band of the underwear until they bounce off of Henry, causing his erection to spring back and tap Jude under his jaw. Henry cries out, and Jude puts a finger up to his lips, turning his attention to Henry’s erection. Henry’s foreskin had still not retracted all the way, only the barest tip of the brilliant purple head was sticking out of the milky white skin. Jude slowly massaged the erection, eliciting a small whimper from Henry with each stroke, until the skin had fully retracted and the air could get to Henry’s glans.

     “So, this is how you do it, kid.”

     Jude gets low enough to blow air onto the tip of Henry’s erection, causing the boy to squirm uncontrollably, Jude chuckles and very slowly sucks Henry into his practiced mouth. He rolls Henry around his mouth for a moment, the skinny three inches Henry is packing is nothing in comparison to what he’s used to, but it’s a nice change of pace. Jude slowly sucks Henry’s balls into his mouth as well, causing the boy to shiver.

     Henry’s balls had dropped, but that was the only sign that puberty was fast approaching on this boy. Jude sucked and nuzzled, his stubble sending ripples through Henry’s body. Suddenly, as if struck by lightning, Henry tenses up, and cries out, almost loud enough to cause worry. Jude sucks and sucks until Henry relaxes fully, and has to sit down on the toilet seat.

     “Wh- what was _that_?”

     “Well, you came.”

     “Bu’ nothin’ came out.”

     “Well, you’re not producing yet. But every time you cum, that feeling you just had? That happens.”

     “Holy _shit._ ”

     “I know right?”

     Jude smiles up at Henry who slowly comes back down from his virginal orgasm. Henry suddenly sits straight up and exclaims.

     “I gotta suck on you too!”

     Jude waves his hand as if to say ‘no worries’.

     “I’m already soft again. Like I said, I’m not that much into kids. But if I get hard again before your train comes, I’ll give you first whack at it.”

     “Promise?”

     “Promise. Now. Let’s get you dressed.”

\------------------------------------------

End Chapter 1

    


	2. Train to Boston

**Summary for the Chapter:**

> Henry meets Jude's cousin, and Jude makes a decent proposal.

Henry sits very close to Jude, surprisingly he was still too nervous around the young man to rest his head on the others shoulder.  Surprising, of course, because about a half an hour earlier, he had seen all of Jude, top to bottom, totally naked.  Maybe that made Henry even more antsy about it.

            Jude sighed and sat back against the bench in the train station, his cousin’s train was delayed by a solid 15 minutes because of some train losing power on the tracks or something.  He didn’t _really_ know, he’d been texting back and forth with his cousin for a while about the train and he was growing mildly annoyed at the time delay.

\--------------------------------------------------------------------------------------------------------------------

I’m waiting in the station still. – **Jude** [8:49am]

[8:50am] **Ian:** ty, but y? Go get breakfast.

Long story.  But I’m kinda trying to make sure someone gets on a train safely. – **Jude** [8:50am]

[8:51am] **Ian:** I’m not the only reason u r @ the station today huh? :-P

Well you were, until I picked up a hitch hiker at a gas station.  He’s 10 and on his way to Boston. - **Jude** [8:52am]

[8:53am] **Ian:** U r such a good samaratan, y does he need 2 go 2 boston?

*Samaritan, and he won’t tell me.  And that’s okay, he doesn’t have to. **-Jude** [8:53am]

[8:54am] **Ian:** Nice & spooky. Maybe he’s a ghost.

He’s not a ghost u butt. **-Jude** [8:55am]

[8:56am] **Ian:** Lol.  If u r so worried about him y don’t we go 2 boston w/ him?

Oh sure Ian, why not just hop on board another train and take the day in boston? Totally not super creepy. **-Jude** [8:58am]

[8:58am] **Ian:** Oh does he think ur creepy?

No. But that’s not the point. **–Jude** [8:59am]

[8:59am] **Ian:** Then just ask him. What’s the harm?

\---------------------------------------------------------------------------------------------------------------------

            Henry had just managed to work up the courage to rest his head on Jude’s arm when Jude spoke.

“Henry?”  Henry startles and sits up straight again.

“Sorry.  I didn’t mean to –“

“What? Oh – no, go ahead, put your head down, I don’t care.  I just have a question for you.”

“Oh.  Oh, okay… what?”

“Would it make you feel more comfortable, on your way to Boston if I tagged along?  My cousin would have to come as well, but I’m just wondering.”  Jude raises an eyebrow and glances up from his phone to gauge Henry’s reaction.

            Henry mulled it over a bit, and knit his brow together.  On one hand, he _really didn’t know these people_.  On the other, _he’d seen one of them naked already_ AND _he could use the company_.  He looks up at Jude with a placid expression.

            “Yeah, that sounds like fun.  Is your cousin going to get here in time for my train?”

            “It’s actually, physically, the same train.  Once it gets here.”  Jude motions to the flip board, the train says ‘arriving in 0:01” which makes him smile, and look over at Henry. “Looks like your train leaving won’t be delayed.”

            “That’s good.”

            Jude suddenly startles and realizes that his car is parked improperly, if he were now to take the train.

            “Ah, damn it.  Okay – Henry.  I gotta go park my car in the garage, now that I’m going with you.  You stay here in case I’m not back in time to see Ian.” Jude starts to move away but then pauses and turns back to Henry, unwrapping his scarf and handing it to the kid. “Here, take this, he’ll recognize it, his dad was the one who gave it to me.  He’s about yay high –“ Jude motions to just over Henry’s head. “Skinny pale kid, blond-ish, lots of freckles.  He’s actually 13, so treat him like a teen, because if you treat him like a kid he gets pissy.  Be right back.”

            Henry blinks a few times as Jude rushes out the door and hops in his car.  As Jude pulls away from the temporary parking spot the bell tolls. _Train arriving on the platform_.  Henry looks around confused, before rooting himself to the spot next to the bench, and watching the people trickle out of the train.  There are only about 20 people or so, and near to the last of them is a nearly vibrating ball of energy.  Medium length strawberry blond hair hangs in shaggy waves and curls on his head, freckles dotting his bright face, a pronounced over bite giving the boy the look as though he is constantly about to speak.  Ian looks around the platform, and wanders into the station, texting with Jude.  He receives a text and looks up expectantly, spying Henry, who waves nervously.  Ian comes bounding over, barely stopping in time to not crash into the other boy.

            “So you’re the hitch hiker, huh?”

            Henry nods quietly, looking the boy up and down.  He was a short boy for his age, but there was enough definition in his exposed arms, to communicate his strength.

            “Got a name?”

            “Henry.  And you’re Ian, yeah?”

            “Yeah.  So we’re goin’ t’ Boston, huh?”

            “Y-yeah.  I guess so.”

            Ian smiles broadly and jumps onto the bench, scanning the surrounding area.

            “Where’s my cousin?”

            “H-he’s parking his car.  He’ll be back in a moment.”

            “Pffft.  Okay – gosh.  This is cool – it’s like one of those adventure movies.”

            Henry laughs nervously.  He wasn’t expecting to be floored by the energy coming off of Ian, but the boy had no off switch, and Henry shifted from foot to foot anxiously.  Ian puffs out his chest and melodramatically exhales.  The announcer comes over the speaker and announces the 1:10 train to South Station is boarding for the next 7 minutes.

            Jude comes jogging back around the corner and spies Henry first, missing his cousin leaping off the bench at him.

            Ian slams into Jude painfully and sends the two crashing to the ground.  Ian recovers first and straddles Jude while tsking at his cousin.

            “You shoulda caught me.”

            Jude just groans and pushes his cousin off of him playfully, getting up and smiling at Henry.

            “Sorry, I didn’t think I would take as long as I did.”

            “I wasn’t worried.”

            “I’m glad… Okay.” Jude motions broadly towards the train platform.  “Are we getting on? Or?”  Ian rolls his eyes and grabs his two suitcases moving towards the train, Henry adjusts his backpack and follows suit, closer to Jude than Ian.  Jude places a welcome hand on Henry’s shoulder.  “You sure you don’t mind us coming with you?”  Henry shakes his head and looks up with a small smile on his lips.

            “I think I’ll be glad of the company.” Jude chuckles at Henry’s annoyingly large vocabulary as the two board the train.

\-------------------------------------

            Ian sits across from Henry, and next to Jude.  He’s been fidgeting for a couple minutes now – he had demanded the window seat, but didn’t realize that would stop him from getting up and moving around the empty train compartment.  However the bonus was he was sitting _very_ close to his favorite cousin.  Close enough to grope – if there weren’t a kid sitting across from them staring out the window.

            Actually, he’s staring out the window.  Why not give it a shot?  Ian slowly crawls his hand up Jude’s knee, towards his crotch, Jude exhales almost angrily through his nostrils.  Ian pauses for a moment before Jude gives an almost imperceptible nod.  Ian smirks and trails his hand to his cousin’s crotch, grabbing it softly, kneading the soft cock he could feel in the fabric.  Jude shifts enough to let Ian grab the full shaft through his jeans, passively flipping through a game on his phone, as if he wasn’t being felt up by his cousin.

            Slowly Ian works his palm into Jude’s crotch, teasing the adults cock until it’s pushing rigidly against the fabric of his jeans, Ian smirks, he can feel the familiar warmth radiating through his cousins body, and was excited that he could turn someone on like that.  Jude gently lowers his phone and clears his throat, getting Henry’s attention, causing Ian to remove his hand from the offending boner.

            “Hey, Henry, remember what I promised earlier?”

            Henry pauses for a moment, biting his lower lip, before his eyes light up with recognition. “Oh! Oh yeah… Is it… um?”

            “Yeah. I’m ready again, are you sure you really wanna try?”

            “Yeah! Yeah! I’m ready too!” He says, his voice cracking a bit in excitement.  Ian squints suspiciously looking between the two before gasping.

            “Oh my God.  Are you two about to do it?”

            “No.” Jude starts

            “Yes!” Henry replies a little offended by Jude’s negation.

            “No, Henry.  We’re not doing it, ‘it’ takes a lot more prep work…” Henry looks confused until Jude explains it to Ian. “He wants me to teach him how to give a blowjob.  It’s nothing butt related.” Ian makes a face and sighs.

            “Coulda told me sooner… He’s cute.” Henry blushes, kicking his feet a little at the praise from the slightly older boy.

            “Well, if Henry’s comfortable with it, you’re more than welcome to join us.” Jude says, sliding out of his seat, and motioning for Henry to follow him to the back of the train car.  Henry glances at Ian and smiles broadly.

            “The more the merrier!” Ian snorts and pops out of the seat as well, trailing behind Henry, like a dog after a bone. “Oh, and you’re cute too.” Henry says, blushing again.  Ian gives him a wink, before pulling him up short, avoiding a collision with Jude.

            “Alright, no camera, and an empty car, c’mon, bathroom’s clear.”  Jude opens the door to a cramped bathroom, one toilet, one urinal, and a window out to the great wide somewhere.  Henry and Ian pile in, before Jude enters and clicks the latch behind them. “Sorry, it’s tighter than I expected.”

            “That’s what they all say” Ian says jokingly, pulling himself up onto the small ledge, where someone’s bag would go, above the toilet.  Now face level with Jude.  Henry scoots back a little to give Jude some room, and presses himself against the back wall, his heart beating quite quickly already.  The smell of two horny boys, and an equally horny man, fills the small bathroom very quickly.  Jude unbuckles his pants, shimmying his jeans off, and tugging his boxers down after, he leans against the door to slide out of his shoes, leaving him in just his socks.

            “Do you want me in what I was wearing before?” Jude asks playfully, Henry just nods, starting to unbutton his own shirt.  Jude complies and gets totally bare, save for his socks, and stands before both boys, cock pointing out into the bathroom, like a guided rocket.

            By the time Henry has finished undressing himself, Jude’s erection has flagged a little, and he tries to jiggle his cock awake, Ian giggles a bit from his perch, sliding down and kissing Jude on the cheek before grabbing the erection from the adult and stroking it dutifully, easily coaxing it back to full mast.  “Mmm, all you needed to do was ask.” Ian says pleasantly, smooching Jude again, before starting to undress himself.  Henry nervously coughs and Jude focuses on the small ten year old, urging him to take a couple steps off the wall, while Ian squirrels himself away on his perch again.

            “Alright, so, unlike last time, take your lips, and go like this…” Jude leans down and shows Henry how to cover his teeth with his lips.  “…It’ll stop your teeth from scraping on my dick, like they did last time.”

            “Is that why you got soft?”

            “Some of the reason, yeah… Okay, show me?” Henry shows off how covered his teeth are and Jude nods satisfactorily. “Alright, now… take it slow, don’t try and fit it all in one go…” He holds his cock by the base, waiting for Henry to take a comfortable position on his knees before slowly moving forwards.

            Henry opens his mouth wide, in anticipation, he feels the head pass by his lips and is startled by how full his mouth already feels.  He adjusts his jaw, keeping his lips covered, and takes another inch, and then another before gagging a little.  Jude stops, starting to pull back, Henry reaches a hand out and stops the adult from pulling out all the way.  “Mmmmgffiidd” Henry assures Jude, adjusting slowly.  He moves of his own volition, letting another couple inches disappear into his prepubescent mouth.  A low whine escapes his throat as he feels the cock head pressing uncomfortably in the back of his jaw, he tries adjusting but after a couple seconds of trying, realizes he can’t get the whole cock in without swallowing some of it.  He steels himself and holds his thumb in his hand, like his mother had taught him how to do in order to brush the back of his tongue without throwing up, and starts swallowing, he feels the cock slide into the very top of his throat, and momentarily panics, wondering if he’ll get enough air just through his nose.  He feels a soothing hand on his head, and looks up, seeing a slightly amazed Jude.

            “Henry, you’re a natural…” Henry smiles despite himself, causing Jude to wince a bit, as Henry’s teeth become exposed.  Henry fixes the situation quickly, and starts to regulate his breathing through his nose. “Ohhh God kid.” Jude moans, feeling the boys throat flexing around his sensitive cock head.

            “Hey, now he’s gotta start moving.” Ian says from his spot, Jude nods a bit, looking back down at the ten year old wrapped around his cock.

            “I-if you’re ready, just start bobbing…”

            “And don’t be afraid to use tongue! He likes tongue.” Ian posits with a slightly jokey voice.  Punctuating the sentence with a sloppy fake kiss sound.

            Henry buckles down and tries to move his tongue around his already full mouth, all the serves to do is cause him to gag, so he stops, pulling back a little and starts to focus just on bobbing up and down, his mouth sliding gracefully along Jude’s spit slicked shaft.  Jude moans despite himself, running his hands through Henry’s hair, and urging the boy to go a little faster.  Henry complies, feeling a bit like a chicken with how fast his head is going forwards and back.  He feels the cock sliding in and out of his throat become easier and easier as the minutes wear on.

            Jude taps Henry’s head three times, and the boy pulls off, gripping the slippery pole with one hand and jacking it while catching his breath.  His face is red with effort, and he’s out of breath, but he feels on top of the world.

            With a grunt Jude cums, thick white ropes oozing out of the enflamed cock and dripping down Henry’s tiny underused hand, one wad catches on Henry’s cheek as Henry gasps in surprise.

            Ian claps, without any hint of sarcasm, and hollers a bit in praise.

            Henry bows his head a bit, looking at the mess on his hand, before tasting it.  He makes a grossed out face and shakes his head a bit.  “NnnmMmm…” He grabs some toiler paper and starts to clean up the mess.

            “Not a fan of cum, huh?” Ian asks, now fully nude, on the ledge.  Henry shakes his head in response, trying to say something, but finding his throat too weak to do much.  “That’s okay, we can’t all be, right cous?”

            Jude nods, he’s out of breath too, his face flushed red with embarrassment, and a little bit of shame.  Ian slides down to the floor, helping Henry find his feet, and getting the preteen up onto the perch he just slide off of.

            “Mmm, while we have you as a captive audience, I wanna show you what a grown ass man can really do…” Ian winks turning to Jude who exhales sharply, realizing what his cousin meant.

            “We talked about this Ian. I don’t think you’re ready…”

            “It’s me, cous, I don’t think it’ll be a problem.” Ian winks and turns back to Henry. “What do ya say Henry, wanna see him fuck me?”

            Henry gapes a bit, eyes wide with shock and wonder, before nodding slowly, building to a fast turn of his head, which causes a mildly dizzy spell.

            “Good… ‘cause that’s what’s coming next.”

            Jude looks warily at Ian, who all but purrs at him, curling a hand around his cousins stained and exhausted cock, and starts kissing at the adults neck…

TBC

**Author's Note:**

> Still a work in progress so I may tweak the language from time to time, and chapter 2 is on the way.


End file.
